#33 2C-I

SYNTHESIS: A mixture of 7.4 g phthalic anhydride and 9.05 g of
2,5-dimethoxyphenethylamine (see the recipe for 2C-H for its
preparation) was heated with an open flame. A single clear phase was
formed with the loss of H2O. After the hot melt remained quiet for a
few moments, it was poured out into a crystallizing dish yielding 14.8
g of a crude solid product. This was recrystallized from 20 mL CH3CN,
with care taken for an endothermic dissolution, and an exothermic
crystallization. Both transitions must be done without haste. After
filtration, the solids were washed with 2x20 mL hexane and air dried
to constant weight. A yield of 12.93 g of
N-(2-(2,5-dimethoxyphenyl)ethyl)phthalimide was obtained as
electrostatic yellow crystals, with a mp of 109-111 °C. A sample
recrystallized from IPA was white, with a mp of 110-111 °C. Anal.
(C18H17NO4) C,H,N.

To a solution of 12.9 g N-(2-(2,5-dimethoxyphenyl)ethyl)phthalimide in
130 mL warm (35 °C) acetic acid which was being vigorously stirred,
there was added a solution of 10 g iodine monochloride in 40 mL acetic
acid. This was stirred for 1 h, while being held at about 30 °C. The
reaction mixture was poured into 1500 mL H2O and extracted with 4x75
mL CH2Cl2. The extracts were pooled, washed once with 150 mL H2O
containing 2.0 g sodium dithionite, and the solvent removed under
vacuum to give 16.2 g of
N-(2-(2,5-dimethoxy-4-iodophenyl)ethyl)phthalimide as yellow amber
solids with a mp of 133-141 °C. This mp was improved by
recrystallization from 75 mL CH3CN, yielding 12.2 g of a pale yellow
solid with mp 149-151 °C. A small sample from a large quantity of IPA
gives a white product melting at 155.5-157 °C.

A solution of 12.2 g
N-(2-(2,5-dimethoxy-4-iodophenyl)ethyl)phthalimide in 150 mL hot IPA
was treated with 6.0 mL of hydrazine hydrate, and the clear solution
was heated on the steam bath. After a few minutes there was the
generation of a white cottage cheese-like solid
(1,4-dihydroxyphthalizine). The heating was continued for several
additional h, the reaction mixture cooled, and the solids removed by
filtration. These were washed with 2x10 mL EtOH, and the pooled
filtrate and washes stripped of solvent under vacuum giving a residue
which, when treated with aqueous hydrochloric acid, gave 3.43 g of
voluminous white crystals. This, after recrystallization from 2
weights of H2O, filtering, washing first with IPA and then with Et2O,
and air drying, gave 2.16 g 2,5-dimethoxy-4-iodophenethylamine
hydrochloride (2C-I) as a white microcrystalline solid, with a mp of
246-247 °C. Anal. (C10H15ClINO2) C,H,N.

DOSAGE: 14 - 22 mg.

DURATION: 6 - 10 h.

QUALITATIVE COMMENTS (with 0 mg) I was present at a group meeting,
but was only an observer. With zero milligrams of 2C-I, I was able to
get to a delightful plus 2.5 in about five minutes after I arrived at
your place, and absorbed the ambience of the folks who had actually
imbibed the material. My level lasted about four hours and came down
at about the same time as did the others. There were no after-effects
experienced except for a pleasant languor.

[Erowid Note: We received several requests for clarification of this note. Alexander Shulgin
confirmed that this experience was a contact-high from being near a group of people
on 2C-I. He writes:

I realize that some readers think that Ann and I are the authors
of all the commentaries but in reality they have come from many
different authors.

I have dug around in my notes and have finally found the
origin of the zero milligram comment. It was a group experiment
with 2C-I. Two members of the group arrived after everyone else had started
and decided not to make a late entry, simply enjoy being
observers. They reported that one of them turned on almost immediately,
and went up to a plus two and a half. Further into his research notes he
wrote that he had "absorbed the ambience of the folks who had
actually imbibed the material," and this was transferred directly
to Pihkal. I hoped that this would make it obvious that it was a
contact high, not a drug-induced high. -- Alexander Shulgin, Oct 2004 personal communication.

We hope that clarifies the issue.]

(with 15 mg) Comfortable onset. Most notable are the visuals,
patterning like 2C-B (Persian carpet type), very colorful and active.
Much more balanced emotional character, but still no feeling of
insight, revelation, or progress toward the true meaning of the
universe. And at 5 1/2 hours drop-off very abrupt, then gentle
decline. I would like to investigate museum levels.

(with 16 mg) There was an immediate alert within minutes. As usual,
it was only an awareness, then nothing happened for a while. In
retrospect, I see some type of activity or awareness within 40
minutes, which then builds up over time. The peak was at 2 hours and
seemed to maintain itself for a while. Near the peak, there was some
hallucinogenic activity, though not a lot. The pictures in the dining
room had color and pattern movement that was fairly detailed.
Focusing on other areas, such as walls or the outside of the house,
produced little activity, though I tried. There was certainly a lot
of color enhancement. There was also that peculiar aspect of the
visual field having darkened or shadowed areas. These darker areas
seemed to shift around to some degree. That aspect seems to be
similar to 2C-B. I don't think I was more than +2.5 at the peak.
Coming down was uneventful. I was down within 6 hours. I had no
problems driving home, nor were there any difficulties with sleep.
There were no body problems with this material. I ate like a horse.

(with 16 mg) The 16 was a bit much, I realized, because my body was
not sure of what to do with all the energy. Next time I'll try 14 or
15. However, my conversations were extremely clear and insightful.
The degree of honesty was incredible. I was not afraid to say
anything to anyone. Felt really good about myself. Very centered, in
fact. A bit tired at day's end. Early bedtime.

(with 20 mg) I think there is slightly less than full immersion in
the sensual, with this material, compared with 2C-B, but I suspect
it's more a matter of getting used to the language of 2C-I and the
feelings--getting tuned to a slightly different frequency, really--
rather than that the material is less sensual or less easy to use
sensually. Just different frequency, and we are very, very used to
2C-B. Good on the body. Transition, for me, not as strongly dark as
2C-B. But it could certainly take a lot more exploring, if we were
able to give the time (about 9 hours) to it. Next day: sleep
excellent. Energy next day unusually good. Quite tired by evening.

EXTENSIONS AND COMMENTARY: The frequent comparisons between 2C-I and
2C-B stem, without doubt, from a bit of chemical suggestion. The two
compounds have structures that are truly analogous, in technical
terms. In one, there is a strategically located iodine atom, and in
the other, an identically placed bromine atom. These are directly
above and below one-another in the periodic table. And what is
particularly maddening to the synthetic diddler, is that they cannot
be lengthened, or shortened, or squooshed around in any way. You
can't make a longer and narrower version of a bromine atom, as you can
do with, say, a butyl group. You've got what you've got, like it or
not. No subtle variations.

But, on the brighter side of the picture, you have a heavy atom here,
and this atom is intrinsic to the central activity of the compound.
So, these materials are naturals for radio-labelling experiments.
2C-I has been made radioactive with radio-iodine, but the most
impressive findings have been made with the 3-carbon analog, DOI.

One quotation from an observer of a group experiment is enclosed; an
experiment with zero milligrams being taken. This is a instructive
observation of what has been called a contact high.

There is one Iodotweetio known. In Scrabble, would you challenge a
word that had seven of its eleven letters as vowels? Especially if
the vowels were, specifically, iooeeio? It sounds just a little like
the noise coming out of Old McDonald's farm. But a Tweetio there is,
namely, the 2-EtO-homologue of 2C-I. This is
2-ethoxy-4-iodo-5-methoxyphenethylamine, or 2CI-2ETO. The
hydrochloride salt was a white, crystalline product with a melting
point of 175-175.5 °C. The threshold level of activity was seen at an
oral dose of 5 milligrams, and the generated effects were completely
dispersed in a couple of hours. Most interestingly, larger doses, of
up to 50 milligrams orally, seem to produce no more intense an effect,
but simply to stretch out this threshold for an additional couple of
hours. At no level that has been tried, has 2CI-2EtO produced even a
plus-two response.

Where else can one go, from 2C-I? The iodine is the fourth, and the
last of the so-called halogens, at the bottom of the classical
periodic table. But, thanks to the miracles that have accompanied us
into the nuclear age, there is a fifth halide now known, Astatine.
All of its isotopes are radioactive, however, and it seems unlikely
that there will ever be an entry (other than this one) for
2,5-dimethoxy-4-astatophenethylamine. What might be speculated as to
its activity? Probably similar in potency to 2C-I, requiring maybe 10
or 20 milligrams. The duration would be dicey to measure, since the
isotope with the longest known half-life is half decayed in about 8
hours, and the longest lived natural isotope (for those who insist on
natural rather than man-made things) is half decayed in less than a
minute. Two predictions would be pretty solid. You might have quite
a job accumulating your 10 milligrams of Astatine, as the most that
has so far been made at one time is only about 0.05 micrograms,
approximately a millionth of the amount needed. And the second
prediction? You would not survive the screaming radiation that would
bombard you if you could get the needed 5 or 10 milligrams of
radio-astatine onto that magic 4-position, and the resulting 2C-A into
your tummy!